Breezy Madeira is an eponymous island in the Madeira Islands, a Portuguese archipelago. The capital city of Funchal was settled in the 15th century and is a colorful collection of gardens, religious sites, and quirky tourist attractions like the thatched-roof Madeira Story Centre. Hike to the summit of Pico Ruivo and you’ll feel like you’ve climbed through the clouds. Unwind over a glass of Madeira wine, an historic fortified beverage that’s musky and subtly sweet.

The Madeira Islands are a stunning archipelago in the middle of the Atlantic — a place of lush greenery and rugged mountains 1,000km from the European mainland. where you can hike in the morning, surf in the afternoon, and finish your day in a fine restaurant where the breathtaking view is complemented by unforgettable Mediterranean or traditional Madeira cuisine.

A coastal town just 20 miles west of Lisbon, Cascais was once a small fishing village, but its idyllic scenery attracted the attention of artists, writers and expelled European nobility in the 20th century. Today, it still attracts high society, but all society comes in force to enjoy the gorgeous beaches and adventure options like sailing and surfing. The Conde de Castro Guimarães Museum, a former palace, is now open to the public and displays an impressive collection of art and artifacts.

Imerovigli looks exactly as a Santorini village should: iconic whitewashed buildings with sapphire domes, narrow crisscrossing walking paths, epic sunsets. Set sail on a guided boat tour of nearby volcanic features or spend the day exploring the remains of Skaros, a 13th-century Venetian palace. Cap it all off with a simple but decadent meal of local delicacies.